US4690838A - Process for enhancing the resistance of a resist image to reactive ion etching and to thermal flow - Google Patents
Process for enhancing the resistance of a resist image to reactive ion etching and to thermal flow Download PDFInfo
- Publication number
- US4690838A US4690838A US06/899,589 US89958986A US4690838A US 4690838 A US4690838 A US 4690838A US 89958986 A US89958986 A US 89958986A US 4690838 A US4690838 A US 4690838A
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- US
- United States
- Prior art keywords
- resist
- alkyl metal
- metal compound
- reactive ion
- ion etching
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
- G03F7/405—Treatment with inorganic or organometallic reagents after imagewise removal
Definitions
- the present invention is concerned with a process for enhancing the resistance of a resist to reactive ion etching and to thermal flow.
- the process of the present invention is broadly applicable to resist images, particularly including photoresist images. It is applicable to many types of resists, including, for example phenolic resins, novolac resins, poly(para-hydroxy styrene), poly(methyl methacrylate) and other acrylate esters, and also copolymers.
- the alkyl metal compounds used in the present invention include dialkyl-magnesium compounds and trialkyl-aluminum compounds, and also other compounds wherein at least one alkyl group is linked to the metal. Examples of these include triethyl aluminum, diisobutyl aluminum hydride, diethoxyethyl aluminum, lithium diisobutyl aluminum hydride, diethyl magnesium and Grignard reagents. Such materials are well known in the art and are commercially available.
- the resist should comprise a polymer which has a group which reacts with the alkyl metal compound to undergo metallation or salt formation.
- the actual contacting of the resist image with the alkyl metal compound may be carried out simply by dissolving the metal alkyl compound in a solvent and dipping the resist image in the solution. Alternatively, the contacting may also be carried out in the vapor state, wherein the alkyl metal compound has been vaporized.
- thermal flow resistance at least up to 250 degrees C., is obtained without any reticulation in large surface areas, such as is often found in prior art methods of treatment.
- a resist image is given increased resistance to reactive ion etching when the etching is carried out using any halogen-containing gases, such as CF 4 , SF 6 and CCl 2 F 2 , and also oxygen as well.
- the resist images can be removed in N-methyl-2-pyrrolidinone after these reactive ion etching treatments.
- Dialkyl-Magnesium Dibutyl-magnesium solution (0.7M in heptane) and diethyl-magnesium solution (0.7M in ether) were used.
- Dibutyl-Magnesium Treatment Images from two types of commercial diazonaphthoquinone novolac matrix resists, with thicknesses of 3.2 ⁇ m and 3.7 ⁇ m respectively, on silicon wafers were dipped into the magnesium solution either for 15 sec or 50 sec, then, immediately into toluene for rinsing. Afterwards, toluene was flushed away with nitrogen stream. The whole process was carried out in a nitrogen atmosphere. The incorporation of magnesium into the resist films was confirmed with ESCA measurements.
- the solution treatment of resist images was carried out by dipping a wafer with resist images into a hexane solution of triethyl aluminum (1.0M solution) for 1 to 4 min at room temperature, followed immediately by rinsing with toluene/heptane, and by nitrogen blowing. The treatment was done in a nitrogen atmosphere. After the nitrogen blowing, the wafer was processed in air.
- Vapor Phase For the vapor-phase treatment a wafer with resist images was placed in a vessel with a rubber septum for an injection of trimethyl aluminum. Then, the vessel was evacuated by a mechanical pump to 50 micron pressure, followed by an injection of trimethyl aluminum solution (1 ml of 1M hexane solution per 500 ml volume). The wafer was kept inside the vessel for one hour at room temperature. Unreacted trimethyl aluminum and hexane were blown off in a nitrogen stream.
- Argon Ion Sputtering Rates and Depth Profiles Depth profiles of these metal atoms in resist films were measured with ESCA and argon ion sputtering, while at the same time the sputtering rate was measured with an Alpha Step 200 thickness measurement instrument. Argon sputtering was carried out in a Plasma Therm diode system under following conditions: incident power of 150 W/11" diameter, -220 V bias potential, 20 sccm, 72 mTorr, 25 C aluminum substrate surrounded by a poly(methyl methacrylate) ring.
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- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Drying Of Semiconductors (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
The reactive ion etching and thermal flow resistance of a resist image is enhanced by contacting the resist image with an alkyl metal compound of magnesium or aluminum.
Description
The present invention is concerned with a process for enhancing the resistance of a resist to reactive ion etching and to thermal flow.
In the manufacture of microcircuits, it is often desired to have resist images which are resistant to thermal flow and which are also resistant to reactive ion etching. In the past, a large amount of research has been done to achieve either or both of these objectives. Some such work is show, for example, in U.S. Pat. Nos. 4,201,800, 4,230,781, 4,259,421 and 4,439,516. See also CHEMICAL ABSTRACTS, Vol. 96:152832t and CHEMICAL ABSTRACTS, Vol. 97:153930f, both 1982.
The prior art methods have obtained some success but they still leave much to be desired, particularly in the area of simultaneously enhancing both the resistance to reactive ion etching and to thermal flow. The prior art also has not been very successful in the treatment of thick resists, particularly bilayer resists. Inspection of the cited prior art makes it obvious that none uses the alkyl metal compounds of the present invention.
According to the present invention, the resistance of a resist image to reactive ion etching and to thermal flow is enhanced by contacting the resist image with an alkyl metal compound of magnesium or aluminum.
The process of the present invention is broadly applicable to resist images, particularly including photoresist images. It is applicable to many types of resists, including, for example phenolic resins, novolac resins, poly(para-hydroxy styrene), poly(methyl methacrylate) and other acrylate esters, and also copolymers.
The alkyl metal compounds used in the present invention include dialkyl-magnesium compounds and trialkyl-aluminum compounds, and also other compounds wherein at least one alkyl group is linked to the metal. Examples of these include triethyl aluminum, diisobutyl aluminum hydride, diethoxyethyl aluminum, lithium diisobutyl aluminum hydride, diethyl magnesium and Grignard reagents. Such materials are well known in the art and are commercially available. In the operation of the process of the present invention, the resist should comprise a polymer which has a group which reacts with the alkyl metal compound to undergo metallation or salt formation.
The actual contacting of the resist image with the alkyl metal compound may be carried out simply by dissolving the metal alkyl compound in a solvent and dipping the resist image in the solution. Alternatively, the contacting may also be carried out in the vapor state, wherein the alkyl metal compound has been vaporized.
By the process of the present invention, thermal flow resistance, at least up to 250 degrees C., is obtained without any reticulation in large surface areas, such as is often found in prior art methods of treatment.
As a result of the present invention, a resist image is given increased resistance to reactive ion etching when the etching is carried out using any halogen-containing gases, such as CF4, SF6 and CCl2 F2, and also oxygen as well. The resist images can be removed in N-methyl-2-pyrrolidinone after these reactive ion etching treatments.
It should be emphasized that the process of the present invention incorporates magnesium or aluminum deeply inside the resist image, i.e., about 1 μm, as measured from ESCA depth profile and Argon sputtering rates. This deep incorporation of metals permits the use of bilayer resists and is one of the unexpected advantages of the present invention.
As possible alternatives to alkyl magnesium and alkyl aluminum reagents, other organometallic reagents will occur to those skilled in the art, provided the metal forms a refractory oxide or fluoride, and reaction occurs with OH and/or ester groups. Esters react readily with alkyl metal compounds of the group IA and IIA metals, while OH groups undergo reaction with the above as well as other alkyl metal reagents, including those of boron, copper, zinc, cadmium, and other transition metals. In addition, the above metals form refractory fluorides and oxides.
The following examples are given solely for purposes of illustration and should not be considered as limitations on the present invention, many variations of which will occur to those skilled in the art without departing from the spirit or scope thereof.
Dialkyl-Magnesium: Dibutyl-magnesium solution (0.7M in heptane) and diethyl-magnesium solution (0.7M in ether) were used.
Dibutyl-Magnesium Treatment: Images from two types of commercial diazonaphthoquinone novolac matrix resists, with thicknesses of 3.2 μm and 3.7 μm respectively, on silicon wafers were dipped into the magnesium solution either for 15 sec or 50 sec, then, immediately into toluene for rinsing. Afterwards, toluene was flushed away with nitrogen stream. The whole process was carried out in a nitrogen atmosphere. The incorporation of magnesium into the resist films was confirmed with ESCA measurements.
Halogen-Based RIE Measurements: As halogen-containing gases, pure SF6 and an 1:1 argon/dichlorodifluoromethane mixture were used. The 15-sec treatment provided 13 times enhancement in SF6 RIE resistance for the diazonaphthoquinone-novolac resist. The similar result was obtained with dichlorodifluoromethane RIE; here, the thickness loss of the magnesium-treated resist films was so small that the enhancement ratio was difficult to assess.
Thermal Flow Resistance: Resist images were treated exactly in the same way as described above. For comparison purpose, uv-hardened images were heated side-by-side with non-treated sample on a hot plate; the surface temperature of the hot plate was 175 degrees C. The untreated sample deformed badly at 175 degrees C. The uv-bonded sample, and also the sample treated by the present invention, showed no deformation at 250 degrees C.
Solution: The solution treatment of resist images was carried out by dipping a wafer with resist images into a hexane solution of triethyl aluminum (1.0M solution) for 1 to 4 min at room temperature, followed immediately by rinsing with toluene/heptane, and by nitrogen blowing. The treatment was done in a nitrogen atmosphere. After the nitrogen blowing, the wafer was processed in air.
Vapor Phase: For the vapor-phase treatment a wafer with resist images was placed in a vessel with a rubber septum for an injection of trimethyl aluminum. Then, the vessel was evacuated by a mechanical pump to 50 micron pressure, followed by an injection of trimethyl aluminum solution (1 ml of 1M hexane solution per 500 ml volume). The wafer was kept inside the vessel for one hour at room temperature. Unreacted trimethyl aluminum and hexane were blown off in a nitrogen stream.
Argon Ion Sputtering Rates and Depth Profiles: Depth profiles of these metal atoms in resist films were measured with ESCA and argon ion sputtering, while at the same time the sputtering rate was measured with an Alpha Step 200 thickness measurement instrument. Argon sputtering was carried out in a Plasma Therm diode system under following conditions: incident power of 150 W/11" diameter, -220 V bias potential, 20 sccm, 72 mTorr, 25 C aluminum substrate surrounded by a poly(methyl methacrylate) ring.
Claims (9)
1. A process for increasing the reactive ion etching and thermal flow resistance of a resist image, said process being characterized by contacting said resist image with a alkyl metal compound of magnesium or aluminum, the resist comprising a polymer which has a group which reacts with the alkyl metal compound to undergo metallization or salt formation.
2. A process as claimed in claim 1 wherein the resist is a photoresist.
3. A process as claimed in claim 1 wherein the resist is a phenolic resin.
4. A process as claimed in claim 1 wherein the resist is a novolac resist.
5. A process as claimed in claim 1 wherein the resist is in a bilayer resist.
6. A process as claimed in claim 1 wherein the alkyl metal compound is a dialkyl-magnesium compound.
7. A process as claimed in claim 1 wherein the alkyl metal compound is a trialkyl-aluminum compound.
8. A process as claimed in claim 1 wherein the contacting is carried out with the alkyl metal compound in a solution.
9. A process as claimed in claim 1 wherein the contacting is carried out with the alkyl metal compound in the vapor state.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/899,589 US4690838A (en) | 1986-08-25 | 1986-08-25 | Process for enhancing the resistance of a resist image to reactive ion etching and to thermal flow |
| JP62126106A JPS6356919A (en) | 1986-08-25 | 1987-05-25 | Resist treatment |
| DE8787108642T DE3779237D1 (en) | 1986-08-25 | 1987-06-16 | METHOD FOR INCREASING THE RESISTANCE OF VARNISHES AGAINST REACTIVE ION WATERING AND HEAT FLOW. |
| EP87108642A EP0261315B1 (en) | 1986-08-25 | 1987-06-16 | A process for enhancing the resistance of a resist image to reactive ion etching and to thermal flow |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/899,589 US4690838A (en) | 1986-08-25 | 1986-08-25 | Process for enhancing the resistance of a resist image to reactive ion etching and to thermal flow |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4690838A true US4690838A (en) | 1987-09-01 |
Family
ID=25411252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/899,589 Expired - Fee Related US4690838A (en) | 1986-08-25 | 1986-08-25 | Process for enhancing the resistance of a resist image to reactive ion etching and to thermal flow |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4690838A (en) |
| EP (1) | EP0261315B1 (en) |
| JP (1) | JPS6356919A (en) |
| DE (1) | DE3779237D1 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762768A (en) * | 1986-01-29 | 1988-08-09 | Macdermid, Incorporated | Thermally stabilized photoresist images |
| US4873176A (en) * | 1987-08-28 | 1989-10-10 | Shipley Company Inc. | Reticulation resistant photoresist coating |
| US5234793A (en) * | 1989-04-24 | 1993-08-10 | Siemens Aktiengesellschaft | Method for dimensionally accurate structure transfer in bilayer technique wherein a treating step with a bulging agent is employed after development |
| US5378502A (en) * | 1992-09-09 | 1995-01-03 | U.S. Philips Corporation | Method of chemically modifying a surface in accordance with a pattern |
| US5776657A (en) * | 1995-03-15 | 1998-07-07 | Ocg Microelectronic Materials, Inc. | Wet-chemical developable, etch-stable photoresist for UV radiation with a wavelength below 200 NM |
| US5885754A (en) * | 1996-05-17 | 1999-03-23 | Mitsubishi Denki Kabushiki Kaisha | Method of forming a pattern |
| US6127089A (en) * | 1998-08-28 | 2000-10-03 | Advanced Micro Devices, Inc. | Interconnect structure with low k dielectric materials and method of making the same with single and dual damascene techniques |
| US20040089406A1 (en) * | 2001-01-16 | 2004-05-13 | Osram Opto Semiconductors Gmbh | Method for producing an etching mask |
| US6989227B2 (en) | 2002-06-07 | 2006-01-24 | Applied Materials Inc. | E-beam curable resist and process for e-beam curing the resist |
| US8592244B2 (en) | 2011-07-25 | 2013-11-26 | International Business Machines Corporation | Pixel sensor cells and methods of manufacturing |
| TWI556068B (en) * | 2014-09-24 | 2016-11-01 | 精微超科技公司 | Methods of laser processing photoresist in a gaseous environment |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59010728D1 (en) * | 1989-04-24 | 1997-07-31 | Siemens Ag | Process for producing etch-resistant structures |
| US4968552A (en) * | 1989-10-13 | 1990-11-06 | International Business Machines Corp. | Versatile reactive ion etch barriers from polyamic acid salts |
| US5275913A (en) * | 1990-05-08 | 1994-01-04 | Industrial Technology Research Institute | Method for preparing resist patterns utilizing solvent development with subsequent resist pattern transfer, via a photo-hardening liquid adhesive, to a receiver substrate and oxygen reactive ion etching |
| DE4029609C2 (en) * | 1990-09-19 | 1994-09-29 | Ind Tech Res Inst | Method for producing a relief image on a substrate |
| US5304453A (en) * | 1991-07-11 | 1994-04-19 | Industrial Technology Research Institute | Method for preparing resist patterns through image layer transfer to a receiver substrate, via a photo-hardening organic liquid adhesive, with subsequent oxygen reactive ion etching |
| US8986562B2 (en) * | 2013-08-07 | 2015-03-24 | Ultratech, Inc. | Methods of laser processing photoresist in a gaseous environment |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201800A (en) * | 1978-04-28 | 1980-05-06 | International Business Machines Corp. | Hardened photoresist master image mask process |
| US4239781A (en) * | 1979-05-03 | 1980-12-16 | Roy Edwards | Method for treating skin ailments |
| US4259421A (en) * | 1979-06-04 | 1981-03-31 | Rca Corporation | Improving etch-resistance of casein-based photoresist pattern |
| US4259369A (en) * | 1979-12-13 | 1981-03-31 | International Business Machines Corporation | Image hardening process |
| US4307178A (en) * | 1980-04-30 | 1981-12-22 | International Business Machines Corporation | Plasma develoment of resists |
| US4439516A (en) * | 1982-03-15 | 1984-03-27 | Shipley Company Inc. | High temperature positive diazo photoresist processing using polyvinyl phenol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090615B1 (en) * | 1982-03-26 | 1989-01-11 | Hitachi, Ltd. | Method for forming fine resist patterns |
| CA1248402A (en) * | 1983-09-16 | 1989-01-10 | Larry E. Stillwagon | Method of making articles using gas functionalized plasma developed layer |
| US4552833A (en) * | 1984-05-14 | 1985-11-12 | International Business Machines Corporation | Radiation sensitive and oxygen plasma developable resist |
| GB2170015A (en) * | 1985-01-11 | 1986-07-23 | Philips Electronic Associated | Method of manufacturing a semiconductor device |
| CA1282273C (en) * | 1985-03-19 | 1991-04-02 | International Business Machines Corporation | Method of creating patterned multilayer films for use in production of semiconductor circuits and systems |
-
1986
- 1986-08-25 US US06/899,589 patent/US4690838A/en not_active Expired - Fee Related
-
1987
- 1987-05-25 JP JP62126106A patent/JPS6356919A/en active Granted
- 1987-06-16 EP EP87108642A patent/EP0261315B1/en not_active Expired
- 1987-06-16 DE DE8787108642T patent/DE3779237D1/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201800A (en) * | 1978-04-28 | 1980-05-06 | International Business Machines Corp. | Hardened photoresist master image mask process |
| US4239781A (en) * | 1979-05-03 | 1980-12-16 | Roy Edwards | Method for treating skin ailments |
| US4259421A (en) * | 1979-06-04 | 1981-03-31 | Rca Corporation | Improving etch-resistance of casein-based photoresist pattern |
| US4259369A (en) * | 1979-12-13 | 1981-03-31 | International Business Machines Corporation | Image hardening process |
| US4307178A (en) * | 1980-04-30 | 1981-12-22 | International Business Machines Corporation | Plasma develoment of resists |
| US4439516A (en) * | 1982-03-15 | 1984-03-27 | Shipley Company Inc. | High temperature positive diazo photoresist processing using polyvinyl phenol |
Non-Patent Citations (2)
| Title |
|---|
| Radiation Chem. Photochem., vol. 96, 1982, Abstract 152832t. * |
| Radiation Chem. Photochem., vol. 97, 1982, Abstract 153930f. * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762768A (en) * | 1986-01-29 | 1988-08-09 | Macdermid, Incorporated | Thermally stabilized photoresist images |
| US4873176A (en) * | 1987-08-28 | 1989-10-10 | Shipley Company Inc. | Reticulation resistant photoresist coating |
| US5234793A (en) * | 1989-04-24 | 1993-08-10 | Siemens Aktiengesellschaft | Method for dimensionally accurate structure transfer in bilayer technique wherein a treating step with a bulging agent is employed after development |
| US5378502A (en) * | 1992-09-09 | 1995-01-03 | U.S. Philips Corporation | Method of chemically modifying a surface in accordance with a pattern |
| US5776657A (en) * | 1995-03-15 | 1998-07-07 | Ocg Microelectronic Materials, Inc. | Wet-chemical developable, etch-stable photoresist for UV radiation with a wavelength below 200 NM |
| US6063549A (en) * | 1995-03-15 | 2000-05-16 | Arch Specialty Chemicals, Inc. | Wet-chemical, developable, etch-stable photoresist for UV radiation with a wavelength below 200 nm |
| US5885754A (en) * | 1996-05-17 | 1999-03-23 | Mitsubishi Denki Kabushiki Kaisha | Method of forming a pattern |
| US6127089A (en) * | 1998-08-28 | 2000-10-03 | Advanced Micro Devices, Inc. | Interconnect structure with low k dielectric materials and method of making the same with single and dual damascene techniques |
| US20040089406A1 (en) * | 2001-01-16 | 2004-05-13 | Osram Opto Semiconductors Gmbh | Method for producing an etching mask |
| US6989227B2 (en) | 2002-06-07 | 2006-01-24 | Applied Materials Inc. | E-beam curable resist and process for e-beam curing the resist |
| US8592244B2 (en) | 2011-07-25 | 2013-11-26 | International Business Machines Corporation | Pixel sensor cells and methods of manufacturing |
| TWI556068B (en) * | 2014-09-24 | 2016-11-01 | 精微超科技公司 | Methods of laser processing photoresist in a gaseous environment |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3779237D1 (en) | 1992-06-25 |
| EP0261315B1 (en) | 1992-05-20 |
| JPS6356919A (en) | 1988-03-11 |
| JPH0427544B2 (en) | 1992-05-12 |
| EP0261315A1 (en) | 1988-03-30 |
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